Fully Biobased Aliphatic Anionic Oligoesters: Synthesis and Properties

<div>The MALDI-TOF MS spectrum of PBDA<sub>70</sub>Ss<sub>30</sub>. <svg height="14.1649pt" id="M39" style="vertical-align:-5.529pt" version="1.1" viewbox="-0.0498162 -8.6359 28.1866 14.1649" width="28.1866pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M541 160L512 170C485 116 462 88 439 67C411 41 376 35 318 35C272 35 238 37 224 48C207 61 205 85 212 121L290 533C305 611 308 615 391 622L397 650H139L133 622C217 615 221 612 206 533L126 118C111 41 103 34 23 26L17 0H474C489 31 528 124 541 160Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,8.294,3.132)"><path d="M309 -142C211 -61 151 99 151 271S210 601 309 683L288 710C141 611 75 451 75 272V271C75 90 141 -72 288 -169L309 -142Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,11.552,3.132)"><path d="M545 403C545 425 527 451 498 451C448 451 400 404 312 286L290 341C262 412 246 451 219 451C182 451 138 404 92 345L112 323C152 368 169 378 181 378C192 378 201 359 216 321L257 214C184 115 142 69 113 69C102 69 93 73 88 79S78 89 68 89C47 89 24 61 24 40C24 8 49 -12 75 -12C125 -12 175 31 271 175L312 64C330 15 357 -12 382 -12C421 -12 475 35 515 98L496 121C466 88 439 62 420 62C402 62 384 92 363 147L325 247C349 280 374 309 397 333C422 361 446 381 462 381C471 381 481 374 488 366C493 360 499 357 505 357C521 357 545 380 545 403Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,16.73,3.132)"><path d="M98 134C72 134 46 117 46 90C46 73 55 65 60 64C95 55 124 32 124 -4C124 -42 95 -68 44 -89L57 -123C122 -104 194 -60 194 22C194 94 136 134 98 134Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,18.886,3.132)"><path d="M563 395C563 428 543 451 519 451C500 451 480 438 472 423C468 415 465 403 470 394C477 381 482 368 482 347C482 272 386 136 342 74H340C334 163 323 257 312 337C302 410 290 451 257 451C214 451 160 385 127 338L145 310C169 341 203 373 209 373C219 373 225 369 232 325C249 215 269 62 271 -15C220 -80 135 -165 18 -231L26 -257L142 -230C254 -105 279 -74 342 13C394 85 484 211 526 286C553 334 563 365 563 395Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,24.23,3.132)"><path d="M283 271C283 451 220 610 70 710L48 683C146 603 207 443 207 271S149 -59 48 -142L70 -169C220 -67 283 90 283 271Z"></path></g></svg> corresponds to linear species oligomer containing hydroxyl end groups with <svg height="6.1673pt" id="M40" style="vertical-align:-0.2063904pt" version="1.1" viewbox="-0.0498162 -5.96091 7.39387 6.1673" width="7.39387pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M536 404C536 423 520 448 491 448C445 448 398 404 308 283L286 338C255 416 242 448 217 448C182 448 138 402 92 341L111 321C149 368 169 378 178 378C188 378 198 363 214 320L254 212C185 117 138 65 107 65C98 65 85 69 82 75C79 82 73 86 65 86C44 86 23 60 23 39C23 7 44 -12 71 -12C119 -12 168 33 265 177L306 61C321 17 347 -12 373 -12C413 -12 465 33 507 96L491 119C459 84 432 60 413 60C395 60 378 92 358 148L321 250C341 279 369 310 389 332C417 363 439 382 456 382C466 382 475 376 481 368C486 361 492 358 496 358C513 358 536 381 536 404Z"></path></g></svg> and <svg height="9.39034pt" id="M41" style="vertical-align:-3.42943pt" version="1.1" viewbox="-0.0498162 -5.96091 7.65486 9.39034" width="7.65486pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M556 393C556 426 537 448 514 448C496 448 478 435 471 420C468 414 462 401 466 394C473 382 480 368 480 346C480 268 392 143 338 67H336C329 163 319 253 309 330S286 448 254 448C215 448 160 383 127 337L143 311C167 344 200 373 208 373S222 365 229 320C246 214 264 66 268 -20C219 -83 131 -171 17 -239L25 -261L137 -235C248 -110 273 -79 335 8C384 77 481 215 520 287C544 332 556 363 556 393Z"></path></g></svg> fatty acid and sulfonated repeating units. <svg height="14.1649pt" id="M42" style="vertical-align:-5.529pt" version="1.1" viewbox="-0.0498162 -8.6359 28.5129 14.1649" width="28.5129pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M645 631C614 643 545 666 457 666C215 666 23 519 23 283C23 90 158 -16 337 -16C412 -16 489 2 522 10C543 39 590 127 606 167L580 181C519 89 459 18 348 18C201 18 122 136 122 287C122 464 244 632 435 632C544 632 602 595 608 472L639 475C643 526 645 581 645 631Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,8.619,3.132)"><path d="M309 -142C211 -61 151 99 151 271S210 601 309 683L288 710C141 611 75 451 75 272V271C75 90 141 -72 288 -169L309 -142Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,11.877,3.132)"><path d="M545 403C545 425 527 451 498 451C448 451 400 404 312 286L290 341C262 412 246 451 219 451C182 451 138 404 92 345L112 323C152 368 169 378 181 378C192 378 201 359 216 321L257 214C184 115 142 69 113 69C102 69 93 73 88 79S78 89 68 89C47 89 24 61 24 40C24 8 49 -12 75 -12C125 -12 175 31 271 175L312 64C330 15 357 -12 382 -12C421 -12 475 35 515 98L496 121C466 88 439 62 420 62C402 62 384 92 363 147L325 247C349 280 374 309 397 333C422 361 446 381 462 381C471 381 481 374 488 366C493 360 499 357 505 357C521 357 545 380 545 403Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,17.055,3.132)"><path d="M98 134C72 134 46 117 46 90C46 73 55 65 60 64C95 55 124 32 124 -4C124 -42 95 -68 44 -89L57 -123C122 -104 194 -60 194 22C194 94 136 134 98 134Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,19.212,3.132)"><path d="M563 395C563 428 543 451 519 451C500 451 480 438 472 423C468 415 465 403 470 394C477 381 482 368 482 347C482 272 386 136 342 74H340C334 163 323 257 312 337C302 410 290 451 257 451C214 451 160 385 127 338L145 310C169 341 203 373 209 373C219 373 225 369 232 325C249 215 269 62 271 -15C220 -80 135 -165 18 -231L26 -257L142 -230C254 -105 279 -74 342 13C394 85 484 211 526 286C553 334 563 365 563 395Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,24.555,3.132)"><path d="M283 271C283 451 220 610 70 710L48 683C146 603 207 443 207 271S149 -59 48 -142L70 -169C220 -67 283 90 283 271Z"></path></g></svg> corresponds to cyclic species oligomer with <svg height="6.1673pt" id="M43" style="vertical-align:-0.2063904pt" version="1.1" viewbox="-0.0498162 -5.96091 7.39387 6.1673" width="7.39387pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M536 404C536 423 520 448 491 448C445 448 398 404 308 283L286 338C255 416 242 448 217 448C182 448 138 402 92 341L111 321C149 368 169 378 178 378C188 378 198 363 214 320L254 212C185 117 138 65 107 65C98 65 85 69 82 75C79 82 73 86 65 86C44 86 23 60 23 39C23 7 44 -12 71 -12C119 -12 168 33 265 177L306 61C321 17 347 -12 373 -12C413 -12 465 33 507 96L491 119C459 84 432 60 413 60C395 60 378 92 358 148L321 250C341 279 369 310 389 332C417 363 439 382 456 382C466 382 475 376 481 368C486 361 492 358 496 358C513 358 536 381 536 404Z"></path></g></svg> and <svg height="9.39034pt" id="M44" style="vertical-align:-3.42943pt" version="1.1" viewbox="-0.0498162 -5.96091 7.65486 9.39034" width="7.65486pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M556 393C556 426 537 448 514 448C496 448 478 435 471 420C468 414 462 401 466 394C473 382 480 368 480 346C480 268 392 143 338 67H336C329 163 319 253 309 330S286 448 254 448C215 448 160 383 127 337L143 311C167 344 200 373 208 373S222 365 229 320C246 214 264 66 268 -20C219 -83 131 -171 17 -239L25 -261L137 -235C248 -110 273 -79 335 8C384 77 481 215 520 287C544 332 556 363 556 393Z"></path></g></svg> fatty acid and sulfonated repeating units. <svg height="17.6175pt" id="M45" style="vertical-align:-6.1814pt" version="1.1" viewbox="-0.0498162 -11.4361 28.1866 17.6175" width="28.1866pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M541 160L512 170C485 116 462 88 439 67C411 41 376 35 318 35C272 35 238 37 224 48C207 61 205 85 212 121L290 533C305 611 308 615 391 622L397 650H139L133 622C217 615 221 612 206 533L126 118C111 41 103 34 23 26L17 0H474C489 31 528 124 541 160Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,7.185,-5.741)"><path d="M310 541L304 571C290 586 211 619 185 610L80 76L131 52L310 541Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,8.294,3.784)"><path d="M309 -142C211 -61 151 99 151 271S210 601 309 683L288 710C141 611 75 451 75 272V271C75 90 141 -72 288 -169L309 -142Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,11.552,3.784)"><path d="M545 403C545 425 527 451 498 451C448 451 400 404 312 286L290 341C262 412 246 451 219 451C182 451 138 404 92 345L112 323C152 368 169 378 181 378C192 378 201 359 216 321L257 214C184 115 142 69 113 69C102 69 93 73 88 79S78 89 68 89C47 89 24 61 24 40C24 8 49 -12 75 -12C125 -12 175 31 271 175L312 64C330 15 357 -12 382 -12C421 -12 475 35 515 98L496 121C466 88 439 62 420 62C402 62 384 92 363 147L325 247C349 280 374 309 397 333C422 361 446 381 462 381C471 381 481 374 488 366C493 360 499 357 505 357C521 357 545 380 545 403Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,16.73,3.784)"><path d="M98 134C72 134 46 117 46 90C46 73 55 65 60 64C95 55 124 32 124 -4C124 -42 95 -68 44 -89L57 -123C122 -104 194 -60 194 22C194 94 136 134 98 134Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,18.886,3.784)"><path d="M563 395C563 428 543 451 519 451C500 451 480 438 472 423C468 415 465 403 470 394C477 381 482 368 482 347C482 272 386 136 342 74H340C334 163 323 257 312 337C302 410 290 451 257 451C214 451 160 385 127 338L145 310C169 341 203 373 209 373C219 373 225 369 232 325C249 215 269 62 271 -15C220 -80 135 -165 18 -231L26 -257L142 -230C254 -105 279 -74 342 13C394 85 484 211 526 286C553 334 563 365 563 395Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,24.23,3.784)"><path d="M283 271C283 451 220 610 70 710L48 683C146 603 207 443 207 271S149 -59 48 -142L70 -169C220 -67 283 90 283 271Z"></path></g></svg> corresponds to linear species oligomer containing ester end groups with <svg height="6.1673pt" id="M46" style="vertical-align:-0.2063904pt" version="1.1" viewbox="-0.0498162 -5.96091 7.39387 6.1673" width="7.39387pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M536 404C536 423 520 448 491 448C445 448 398 404 308 283L286 338C255 416 242 448 217 448C182 448 138 402 92 341L111 321C149 368 169 378 178 378C188 378 198 363 214 320L254 212C185 117 138 65 107 65C98 65 85 69 82 75C79 82 73 86 65 86C44 86 23 60 23 39C23 7 44 -12 71 -12C119 -12 168 33 265 177L306 61C321 17 347 -12 373 -12C413 -12 465 33 507 96L491 119C459 84 432 60 413 60C395 60 378 92 358 148L321 250C341 279 369 310 389 332C417 363 439 382 456 382C466 382 475 376 481 368C486 361 492 358 496 358C513 358 536 381 536 404Z"></path></g></svg> and <svg height="9.39034pt" id="M47" style="vertical-align:-3.42943pt" version="1.1" viewbox="-0.0498162 -5.96091 7.65486 9.39034" width="7.65486pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M556 393C556 426 537 448 514 448C496 448 478 435 471 420C468 414 462 401 466 394C473 382 480 368 480 346C480 268 392 143 338 67H336C329 163 319 253 309 330S286 448 254 448C215 448 160 383 127 337L143 311C167 344 200 373 208 373S222 365 229 320C246 214 264 66 268 -20C219 -83 131 -171 17 -239L25 -261L137 -235C248 -110 273 -79 335 8C384 77 481 215 520 287C544 332 556 363 556 393Z"></path></g></svg> fatty acid and sulfonated repeating units. <svg height="17.6175pt" id="M48" style="vertical-align:-6.1814pt" version="1.1" viewbox="-0.0498162 -11.4361 28.1866 17.6175" width="28.1866pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M541 160L512 170C485 116 462 88 439 67C411 41 376 35 318 35C272 35 238 37 224 48C207 61 205 85 212 121L290 533C305 611 308 615 391 622L397 650H139L133 622C217 615 221 612 206 533L126 118C111 41 103 34 23 26L17 0H474C489 31 528 124 541 160Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,7.185,-5.741)"><path d="M310 541L304 571C290 586 211 619 185 610L80 76L131 52L310 541Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,10.223,-5.741)"><path d="M310 541L304 571C290 586 211 619 185 610L80 76L131 52L310 541Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,8.294,3.784)"><path d="M309 -142C211 -61 151 99 151 271S210 601 309 683L288 710C141 611 75 451 75 272V271C75 90 141 -72 288 -169L309 -142Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,11.552,3.784)"><path d="M545 403C545 425 527 451 498 451C448 451 400 404 312 286L290 341C262 412 246 451 219 451C182 451 138 404 92 345L112 323C152 368 169 378 181 378C192 378 201 359 216 321L257 214C184 115 142 69 113 69C102 69 93 73 88 79S78 89 68 89C47 89 24 61 24 40C24 8 49 -12 75 -12C125 -12 175 31 271 175L312 64C330 15 357 -12 382 -12C421 -12 475 35 515 98L496 121C466 88 439 62 420 62C402 62 384 92 363 147L325 247C349 280 374 309 397 333C422 361 446 381 462 381C471 381 481 374 488 366C493 360 499 357 505 357C521 357 545 380 545 403Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,16.73,3.784)"><path d="M98 134C72 134 46 117 46 90C46 73 55 65 60 64C95 55 124 32 124 -4C124 -42 95 -68 44 -89L57 -123C122 -104 194 -60 194 22C194 94 136 134 98 134Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,18.886,3.784)"><path d="M563 395C563 428 543 451 519 451C500 451 480 438 472 423C468 415 465 403 470 394C477 381 482 368 482 347C482 272 386 136 342 74H340C334 163 323 257 312 337C302 410 290 451 257 451C214 451 160 385 127 338L145 310C169 341 203 373 209 373C219 373 225 369 232 325C249 215 269 62 271 -15C220 -80 135 -165 18 -231L26 -257L142 -230C254 -105 279 -74 342 13C394 85 484 211 526 286C553 334 563 365 563 395Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,24.23,3.784)"><path d="M283 271C283 451 220 610 70 710L48 683C146 603 207 443 207 271S149 -59 48 -142L70 -169C220 -67 283 90 283 271Z"></path></g></svg> corresponds to linear species containing acid end groups with <svg height="6.1673pt" id="M49" style="vertical-align:-0.2063904pt" version="1.1" viewbox="-0.0498162 -5.96091 7.39387 6.1673" width="7.39387pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M536 404C536 423 520 448 491 448C445 448 398 404 308 283L286 338C255 416 242 448 217 448C182 448 138 402 92 341L111 321C149 368 169 378 178 378C188 378 198 363 214 320L254 212C185 117 138 65 107 65C98 65 85 69 82 75C79 82 73 86 65 86C44 86 23 60 23 39C23 7 44 -12 71 -12C119 -12 168 33 265 177L306 61C321 17 347 -12 373 -12C413 -12 465 33 507 96L491 119C459 84 432 60 413 60C395 60 378 92 358 148L321 250C341 279 369 310 389 332C417 363 439 382 456 382C466 382 475 376 481 368C486 361 492 358 496 358C513 358 536 381 536 404Z"></path></g></svg> and <svg height="9.39034pt" id="M50" style="vertical-align:-3.42943pt" version="1.1" viewbox="-0.0498162 -5.96091 7.65486 9.39034" width="7.65486pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M556 393C556 426 537 448 514 448C496 448 478 435 471 420C468 414 462 401 466 394C473 382 480 368 480 346C480 268 392 143 338 67H336C329 163 319 253 309 330S286 448 254 448C215 448 160 383 127 337L143 311C167 344 200 373 208 373S222 365 229 320C246 214 264 66 268 -20C219 -83 131 -171 17 -239L25 -261L137 -235C248 -110 273 -79 335 8C384 77 481 215 520 287C544 332 556 363 556 393Z"></path></g></svg> fatty acid and sulfonated repeating units.</div>

International Journal of Polymer Science

fig7

Figure 7

Figure 7: Fully Biobased Aliphatic Anionic Oligoesters: Synthesis and Properties 